ISN: In Ten
Jack Vander Leeuw On Why the Alpha Lives Between Essential Businesses and AI
Jack Vander Leeuw is the Founder & Managing Partner of Token Capital Group, a Charlotte-based Independent Sponsor focused on the intersection of demand-resilient businesses and AI-driven operational transformation. Token Capital Group targets platform acquisitions in the $20–75M enterprise value range.
ISN: In Ten is a new short interview series from Independent Sponsor News spotlighting the people building, backing, and transacting across the Independent Sponsor ecosystem. Ten questions designed to capture experience, conviction, and current views on the market - answered directly, without the polish.
Introducing: Jack Vander Leeuw
Jack Vander Leeuw didn't leave the institutional world because it wasn't working. He left because he could see where it was headed - and he wanted to be ahead of it.
Over 15 years at Capitala Group, he did the work most people spend careers building toward: 42 platform transactions, north of $2.7 billion in enterprise value, operating across both private equity and private credit in the lower middle market.
Vander Leeuw sat on both sides of the capital structure. He watched deals compound and deals fail. And over time, a pattern became impossible to ignore: The businesses that consistently created value weren't the most sophisticated, the fastest-growing, or the best-marketed. They were the ones where customers bought because they had to, and where the operations, still largely manual and largely untouched, had a ceiling that was about to get dramatically higher.
That ceiling is AI.
In 2026, Vander Leeuw founded Token Capital Group in Charlotte, NC around what he calls the Intersection Thesis: acquire essential businesses where customer demand is structural and non-discretionary, then unlock the operational upside that institutional capital has overlooked and that AI makes newly accessible. The firm targets platform acquisitions in the $20–75 million enterprise value range, pursuing businesses where physical products, physical movement, or physical work is required -sectors where manual operations are the norm and where the right buyer hasn't yet arrived with the tools to transform them.
Token is, by design, a firm of one - for now. Vander Leeuw describes his team size as "1 human + lots of AI," a line that reads as a joke until you understand the thesis behind it. AI isn't a feature at Token. It's the operating system. Before an LOI is submitted, a sequenced value creation plan is already mapped to the target's specific operational levers.
The transformation work starts in diligence, not post-close.
The thesis is specific. The universe is narrow by design. And Vander Leeuw is patient enough to wait for the right intersection, because he believes that's where the alpha lives.
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Interview Q&A
1. You spent over 15 years doing this work at the institutional level. What made you decide the time was right to go out on your own?
"I spent over 15 years doing this work at the institutional level: 42 transactions, north of $2.7 billion in enterprise value, seats on both sides of the capital structure. That experience gave me a very clear view of where the lower middle market is headed and what it will take to compete. I started Token Capital Group because I saw a convergence forming between demand-resilient businesses and AI that almost no one in the independent sponsor space is equipped to act on. The conviction got too strong to ignore taking action."
2. Token Capital Group is built around a specific conviction: that businesses pairing demand-resilient operations with AI-driven execution will structurally outperform. Where did that thesis come from?
"It came from pattern recognition across dozens of deals. The businesses that consistently compounded value shared two traits: their customers bought because they had to, not because they wanted to, and their operations had enormous room for improvement. AI changed the equation on that second dimension. Suddenly the ceiling on what you could do operationally inside a lower middle market company got dramatically higher, and almost nobody in the space had the fluency to capture it."
3. The firms you're targeting must be open to real operational change. How do you assess whether a management team is genuinely ready for that?
"I listen for curiosity more than expertise. A management team does not need to understand the technical intricacies of AI. They need to be honest about where time gets wasted, where decisions are made on gut feel, and where they know they are leaving value on the table. If they are protective or complacent of the inefficiency, that tells me everything. If they are frustrated by the inefficiency and want to see change, we can work together."
4. What does "practitioner-level AI fluency" look like inside a deal process - what are you doing differently from day one that a traditional sponsor isn't?
"Before I submit an LOI, I will already have a sequenced AI value creation plan mapped to specific operational levers in the target business. I am not outsourcing that step to a consultant post-close to check-the-box. I built this firm with AI as the foundational operating system so I can underwrite the transformation opportunity with the same rigor I apply to the financials."
5. How do you identify whether a business has the operational foundation to genuinely benefit from AI transformation versus one where it would be disruptive or counterproductive?
"I evaluate six specific value levers: back-office automation, customer intelligence, dynamic pricing, workforce augmentation, predictive operations, and the data flywheel. A target needs clear applicability across at least three of those to qualify. But the real filter is whether the core demand is immune to digital substitution. AI should transform how the work gets done, not call into question whether the work needs doing at all."
6. You describe Token's role as navigating change in a way that's "productive, transformative, and humane." What does that mean to you as an investor?
"It means I tell sellers and management teams the truth: AI is going to reshape their business whether I am the buyer or not. My objective is to successfully steward the business through that change while making the existing employees more effective, capable, and productive. However, I do not make promises I cannot keep about preserving every role. I make promises about how I will conduct myself throughout the process. That honesty is what earns trust and buy-in from the team, which is what makes organizational-wide AI adoption actually work."
7. What types of businesses or sectors are you most focused on right now, and why do they fit the intersection you're building toward?
"I target essential businesses where physical products, physical movement, or physical work is required, where operations are still largely manual, and where institutional capital has not yet compressed valuations. The specifics of the sector matter less than those three conditions being present. When they are, you get a business with a structural floor under demand and a very high ceiling on what AI can unlock operationally."
8. When raising capital deal-by-deal, how do you find partners who genuinely understand what Token is doing - and what does that alignment look like in practice?
"I have spent my career building relationships with institutional equity and credit providers who have already done deals with [me]. They know who they are backing and I know how they like to operate. Additionally, every investment committee on the planet right now is asking, 'How will AI impact this business?' Alignment means they are not just providing capital, they see the AI transformation opportunity as the value creation engine, not a risk factor."
9. What's the hardest part of launching a firm with a thesis this specific?
"Patience. The thesis narrows the universe by design, and that is the point. The temptation is to widen the aperture when deal flow is slower than you would like. The discipline is knowing that the intersection of enduring demand and intelligent automation is where the alpha lives, and that the worst thing I could do is compromise on that conviction to get a deal done faster."
10. What does success look like for Token Capital Group five years from now - what would tell you the conviction was right?
"A portfolio of 5+ businesses that are measurably more competitive, more efficient, and more valuable than when we acquired them, with management teams that are aligned with the process, and happy investors. To me, that would be a track record that validates the conviction and proves the thesis."
BONUS: What didn't we ask that you actually wanted to answer?
"Nobody asks about the human side, and it is one of the parts I think about the most. Having bought businesses from founders and worked with management teams directly before, I know how much they treasure their legacy and their people. AI will reshape workforces. That is not a maybe. The question that defines the next decade of private equity is not who can deploy AI the fastest, but who can do it in a way that the people inside these businesses actually trust. I believe that is a real and durable competitive advantage, and it is central to everything we are building at Token."
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